If they don't learn the soft way now they are going to learn the hard way later when the main org take away their admin privileges from their hands and restrict them to the php app.
The IT team is quite fed up with the incessant problems of this server (mail gateway got blacklisted for instance with the last incident). That server should have been retired but our resident guru has hit a mental roadblock regarding the migration.
I can't format the word enough so here it is with capital letters: DOCUMENTING.
> take over your "superior" variant of technical debt
Clearly the current server situation (one guy knows how to run it) is vastly superior to documenting it for others and not patching security holes is okay.
At least now we'll be able to shut down a particular service instead of shutting down the whole dept. next time that server hiccups.
How many other individuals in this clearly legacy organization have the knowledge and experience to take over your "superior" variant of technical debt once you get sick of the job and move to something trendier?